Oxidation of 1-aminobenzotriazole with N-bromosuccinimide and with nickel peroxide generates benzyne in high and in low yield, respectively. With nickel peroxide, other metal oxides, and iodobenzene diacetate, a variety of products, including azobenzene, benzo[c]cinnoline, 1-phenylbenzotriazole and mono- and di-phenyldihydrodibenzotetra-azapentalenes are obtained. Mechanisms involving benzyne and nitrene intermediates are proposed for their formation.